Lights, camera, action!
What light through yonder film screen breaks? It is the beginning of Shakespeare in Love, which tells us that it's 1593.
We're backstage of the Rose, an Elizabethan theater, and there's more drama backstage than there is onstage. The Rose's owner, Philip Henslowe, is being tortured by his financier, Mr. Hugh Fennyman, who's lighting a fire under Henslowe's feet.
Literally.
Henslowe isn't good at managing money, but he swears he's good at managing talent. He promises a new play soon, one sure to fill seats: a comedy by William Shakespeare called Romeo and Ethel, the Pirate's Daughter.
Hmmm… sounds like it could use a bit of editing.
But first, it could use a bit of writing. William Shakespeare, a dreamy lad, needs a muse. He thinks it might be Rosaline, seamstress to actor William Burbage, but when he catches her in bed with Mr. Tilney, the Master of Revels, their writer/muse relationship is kaput. Where's he going to look now? He can't put an ad on Craigslist looking for a muse. (Note: Don't ever answer an ad on Craigslist looking for a muse.)
Depressed, Will drinks away his sorrows. In the pub, he meets fellow playwright Christopher Marlowe, who gives him a few revisions for his play. Romeo is a lovesick Italian, in love with a girl he cannot be with, etc. etc. It's starting to sound like the play we're familiar with. But who will play Romeo?
Enter Viola de Lesseps. If that doesn't sound like a man's name, it's because it isn't. Viola wants to be an actor in a time where women aren't allowed on stage. So she straps down her chest, puts on some boy's clothes, changes her name to Thomas Kent, and auditions for the role of Romeo. Will is entranced. Could Shakespeare be falling for Romeo?
He follows Kent to the de Lesseps estate where a party is in full swing. There he meets Viola, who is simply gorgeous (and female), and Will falls hard for her. However, Viola is engaged (against her will) to Lord Wessex, who wants to know why this scrawny little writer keeps dancing with his woman. Will tells Wessex his name is "Christopher Marlowe" and flees.
But he meets Viola on her balcony, and their interaction is so romantic that someone should it in a play. Hey, that's an idea. Will rushes home to write new scenes, using Viola (who, unbeknownst to Will, is his Romeo) as inspiration for his Juliet. A theater troupe called the Admiral's Men, led by Ned Alleyn, joins the play, and Viola-as-Thomas takes the role of Romeo.
But Romeo, Romeo, wherefore art thou so sad?
Lord Wessex has decided to marry Viola in two weeks and take her to the Colony of Virginia. Viola-as-Thomas delivers a letter to Will from Viola-as-Viola forbidding him from pursuing their relationship further.
If you know anything about Shakespeare, it's that he loves him some forbidden love. This prompts him to chase down Thomas Kent, who finally reveals that he is actually Viola. Just to make sure, Will goes to her room and takes off all her boy's clothes. Yep, there's a woman underneath all that.
And so begins their passionate love affair. This includes kissing, writing, and other things ending in –ing, including visiting the Queen. Did we mention kissing? Shakespeare in Love even took home MTV's Best Kiss award in 1999 (source).
Anyway, Queen Elizabeth I is interrogating Wessex's bride-to-be. She's shocked that Viola loves poetry and plays so much. The Queen doesn't believe that a play can accurately portray love: "Playwrights teach nothing about love, they make it pretty, they make it comical, or they make it lust. They cannot make it true."
A bet is made that someone can do it. William Shakespeare, perhaps? The pressure is on for him to write more, and write better.
All the while, though, a deadline looms: Viola's wedding to Lord Wessex. They know their affair has a short lifespan. It ends up being cut even shorter when Christopher Marlowe turns up dead, and Will thinks that (a) Wessex killed Marlowe and (b) he's responsible. He slips into a deep grief. Plus, Viola finds out Shakespeare has an estranged wife, Anne Hathaway. (No. Really. Her name is Anne Hathaway, and she's in Stratford-Upon-Avon, not off filming The Princess Diaries 3.)
However, it's revealed that Wessex didn't kill Marlowe… but he still wants William Shakespeare dead. They duel in an epic swordfight on the stage of the Rose while Viola, as Thomas, watches helplessly. It ends in a draw, and Wessex leaves. However, Mr. Tilney, Master of Revels, enters and shuts down the Rose for lewdness. He says there's a woman acting on stage, and Thomas's true identity is revealed. Viola had been ratted out by a grubby little street urchin who had been fired from the play.
Now Shakespeare has lost his Romeo, and he will soon lose his real-life Juliet. Viola is wed to Lord Wessex, but she learns that the play is being performed at a different theatre, the Curtain, and she sneaks away to watch it. With Viola expelled from the theatre, Will steps into Romeo's breeches. And backstage, the young boy to play Juliet is going through a voice change. His voice is too deep to play the maiden, so the play is suddenly without a Juliet.
Whose light through yonder window will break?
Viola finds out there is no Juliet, and she steps in to play the role. A woman playing a woman. Scandalous! But, with Will as Romeo and Viola as Juliet, the play is a smash hit. Not only does the public love it, but so does the Queen, who somehow snuck in even though she's wearing a truly gigantic dress. When Mr. Tilney tries to get the Curtain shut down too, for having a woman on stage, the Queen lies for Viola, saying that Viola is a man, Thomas Kent, who is just really really good at looking like a woman.
Most importantly, the Queen declares that a playwright has finally portrayed true love, cementing Romeo and Juliet's reputation as a timeless play. However, she tells Thomas Kent to go fetch Lord Wessex's bride. She may have gotten to be an actor for a day, but Viola still must go to the United States with a man she does not love.
Viola and Will says a tearful goodbye, but not before brainstorming his next play, one in which a woman named Viola is the sole survivor of a shipwreck. The Queen wants it performed for Twelfth Night, which sounds like a really catchy title, too. Viola and Will say they will love each other always. Viola departs, and Will beings to write again.